[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:12]([CH:15]=[C:16]1[NH:21][CH2:20][CH2:19][CH2:18][S:17]1)([O-:14])=[O:13].C(N(CC)CC)C>O1CCCC1>[C:1]1([CH2:7][S:8]([N:21]2[CH2:20][CH2:19][CH2:18][S:17][C:16]2=[CH:15][N+:12]([O-:14])=[O:13])(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1A solution of 2.29 g of phenylmethanesulfonyl chloride in 20 ml of tetrahydrofuran was added drop-by-drop to a stirred slurry of 1.6 g of 2-(nitromethylene)-tetrahydro-2H-1,3-thiazine and 2.02 g of triethylamine in 10 ml of dry tetrahydrofuran at -50° C. The resulting mixture was stirred at -50° C. for 1 hour, 1.0 g of phenylmethanesulfonyl chloride was added, and the mixture was stirred for a further hour. The mixture was partitioned between methylene chloride and water. The organic phase was separated, washed with water and brine, dried (MgSO4) and stripped of solvent. The residue was flash chromatographed over silica gel, using methylene chloride as eluent, to give N-(phenylmethylsulfonyl)-2-(nitromethylene)-tetrahydro-2H-1,3-thiazine (5A), as a pale yellow solid, m.p.: 140°-141° C.
Wird geladen…
